Chapter 8. The Big Leagues

The day-to-day job of a senior manager depends greatly on the company you’re in. It would be silly of me to say that my job running a startup engineering organization of 70 people was the same as the job held by a senior manager who’s over thousands of people at a Fortune 500 company. Books upon books upon books are written about senior management at scaled companies from a general perspective. I’ve listed some recommended reading at the end of this chapter for general-purpose senior leadership advice. All of these books are fantastic and essential guidelines for senior leaders.

But we’re not general-purpose senior leaders. We’re technology senior leadership. This book is for the engineer who wrote code for a while and eventually moved into management, and successfully grew a career up along that path. And as engineers, we share some common responsibilities that are specific to our role as technologists and come partially from our upbringing working in that ever-changing world.

As technical senior managers, we bring special skills to an organization. In particular, we bring a willingness to embrace and drive change as needed. We’re able to question the way we do things now, and try different things if our current way of operating isn’t working. We understand that technology evolves quickly, and we want our organizations to evolve to keep up with these changes. We have a unique role, but we still need to succeed in our general senior management roles. It’s not enough to be a change agent; we have to create an organization that can successfully follow through on the changes we want to push.

Your first job is to be a leader. The company looks to you for guidance on what to do, where to go, how to act, how to think, and what to value. You help set the tone for interactions. People join the company because they believe in you, in the people you hired, and in the mission you helped to craft.

You’re capable of making hard decisions without perfect information and willing to face the consequences of those decisions.

You’re capable of understanding the current landscape of your business, as well as seeing into its many potential futures. You know how to plan for the months and years ahead so that your organization is best suited to handle those potential futures and capture opportunities as they come along.

You understand organizational structure and how it impacts the work of teams. You know the value of putting in place management that strengthens this structure rather than undermining it.

You can play politics in a productive way, in order to move the organization and the business forward. You work well with your peers outside of engineering and seek out their perspectives in addressing issues with a wide scope.

You understand how to disagree with a decision and commit to deliver on it even though you disagree.

You know how to hold individuals and organizations accountable for their output.

In his book High Output Management,¹ Andy Grove breaks down management tasks into four general categories:

Sitting in meetings, reading and writing emails, talking to people one on one, gathering perspectives. The strong senior leader is capable of synthesizing large quantities of information quickly, identifying critical elements of that information, and sharing the information with the appropriate third parties in a way they will be able to understand.

Reminding people of their commitments by asking questions instead of giving orders. It’s hard for a leader of a large team to forcefully guide that team in any direction, so instead rely on nudging members of the team to keep the overall organization on track.

Taking conflicting perspectives and incomplete information and setting a direction, knowing that the consequences of a poor decision will impact both you and possibly the whole team. If making decisions were easy, there would be much less need for managers and leaders. However, as anyone who has spent a lot of time managing can tell you, making decisions is one of the most draining and stressful parts of the job.

Showing people what the values of the company are. Showing up for your commitments. Setting the best example for the team even when you don’t feel like it.

Whether you’re a CTO, a VP, a general manager, or a head of engineering, your days are shaped by those four tasks.